Oxalyl chloride → 3,4-Difluorobenzenepropanoyl chloride

HRID 547657Notes

Reaction equation

HRID 547657 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:13])C(O)=O)[CH:5]=[CH:6][C:7]=1[F:8].C(Cl)(=O)[C:15]([Cl:17])=[O:16]>CN(C)C=O.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:13][C:15]([Cl:17])=[O:16])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 20668528444170-17-6

Product 1

HCID 575859753,4-Difluorobenzenepropanoyl chlorideYield 99.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (200 mL) containing 3,4-difluorophenyl propionic acid (30.45 g, 163.6 mmol) and 2 drops of dimethylformamide was added oxalyl chloride (41.4 g, 327.1 mmol) over 20 min. The resulting solution was stirred for 24 hours at which time the solvent was removed in vacuo. The residual oil was then evaporated with toluene (˜100 mL) yielding 33.4 g of 3-(3,4-difluorophenyl)propanoyl chloride as a yellow liquid, which was taken directly into the next step.

Workup

  1. customwas removed in vacuo
  2. customThe residual oil was then evaporated with toluene (˜100 mL)

Sources & evidence

ORD record
ord-4b9e394351084ce69d52571f6696f391
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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